Reaktion #987524

Reaktionsgleichung

sodium carbonate

4-formylphenylboronic acid

4-(4-bromophenyl)-dibenzofuran

→

title compound

4′-Dibenzofuran-4-yl-biphenyl-4-carbaldehyde

Lösungsmittel

toluene

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was heated to 100® C
2. 2
   Sonstigepartitioned between water and ethyl acetate
3. 3
   SonstigeThe phases were separated
4. 4
   Extraktionthe aqueous phase being further extracted with ethyl acetate (2×20 mL)
5. 5
   ExtraktionThe combined extract
6. 6
   Waschenwas washed with 0.5 N hydrochloric acid, water and brine
7. 7
   Trocknendried over anhydrous MgSO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigePurification of the product by flash column chromatography

Vorschrift

A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4-(4-bromophenyl)-dibenzofuran (from the previous reaction) in toluene (40 mL). tetrakis-(Triphenylphosphine)palladium(0) (270 mg, 5 mol %) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added and the reaction was heated to 100® C. (oil bath temp.) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2×20 mL). The combined extract was washed with 0.5 N hydrochloric acid, water and brine and then dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 10-20% ethyl acetate in hexane as eluent, afforded the title compound has a white solid (1.51 g).

Quelle